Toluene → 2-Fluoro-4-(2,4-dichlorophenyl)benzonitrile

HRID 498971Notes

Reaction equation

HRID 498971 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1B(O)O.Br[C:13]1[CH:20]=[CH:19][C:16]([C:17]#[N:18])=[C:15]([F:21])[CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O.C(O)C>[F:21][C:15]1[CH:14]=[C:13]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[CH:20]=[CH:19][C:16]=1[C:17]#[N:18]

Participants

8

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 7360294-Bromo-2-fluorobenzonitrileHCID 2734659(2,4-Dichlorophenyl)boronic acid

Product 1

HCID 221708972-Fluoro-4-(2,4-dichlorophenyl)benzonitrileYield 94%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1.0 g (5.2 mmol) of 2,4-dichlorophenylboronic acid, 1.1 g (5.5 mmol) of 4-bromo-2-fluorobenzonitrile, 1.6 g (15.0 mmol) of sodium carbonate and 0.8 g (0.7 mmol) of tetrakis(triphenylphosphine) palladium were added to a solvent mixture of 50 ml of toluene, 25 ml of ethanol and 25 ml of water, and the reaction was carried out under reflux with heating for 2 hours. The reaction mixture was poured into ice-cold water and extracted with toluene. The toluene layer was washed with water twice and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 1.3 g of 2-fluoro-4-(2,4-dichlorophenyl)benzonitrile (yield 93.0%), which was used in Example 8 (1) as the starting material.

Workup

  1. temperatureunder reflux
  2. temperaturewith heating for 2 hours
  3. additionThe reaction mixture was poured into ice-cold water
  4. extractionextracted with toluene
  5. washThe toluene layer was washed with water twice
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-86dcc9b859f34b799c80b133dbbf25f6
Source dataset
uspto-grants-2010_08
Patent number
US07767626B2

Reaction notes

Loading…